As part of a larger study, this paper describes teachers' perspectives and strategies on including overweight and obese students (OWS) in instruction related to motor skill/game play and fitness development in physical education. Using the Social Ecological Constraints framework, a qualitative multicase study was conducted using multiple in-depth interviews, class observations, and artifacts from nine experienced and committed suburban middle school Physical Education teachers. Constant comparison was used to generate themes and trustworthiness procedures were used to confirm findings. Two types of strategies for including OWS in instruction were identified: First-order and Second-order. School resources, shared program goals, and beliefs about students and teaching were factors influencing teachers' decisions and actions for teaching motor skill/game play and fitness content to OWS.